


Does it Really Feel Good?

by Anonymous



Category: Supernatural
Genre: Accidental Voyeurism, Anal Fingering, Awkward situations, Bisexual Dean Winchester, Bisexual Sam Winchester, Drinking to Cope, First Time, Incest, M/M, Masturbation, Some things may be read as homophobia or internalized homophobia, but it’s more a lack of knowledge than malicious intent to be an ass, sexuality questioning
Language: English
Status: Completed
Published: 2019-06-03
Updated: 2019-06-03
Packaged: 2020-04-07 03:45:45
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,009
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19076827
Author URL: https://archiveofourown.org/
Summary: Dean walks in on Sam with his fingers in his ass, and promptly panics over it.





	Does it Really Feel Good?

Dean returned from a supply run to find the bunker quiet and empty. The quietness wasn’t necessarily unusual, because Sam was normally in the library researching, but Dean had checked the library and the kitchen and hadn’t seen Sam. He hadn’t noticed any notes or missing cars to indicate Sam had left. At first he’d just wanted to find Sam to let him know he’d gotten him more of that fancy shampoo he likes, but Dean was starting to get really worried. He finally decided to check Sam’s room. He probably should’ve checked there sooner, but it was weird for Sam to be in his room in the middle of the day. 

When he rounded the corner to the hallway with their bedrooms, he immediately noticed that Sam’e door is cracked. He quietly approached the door and pushed it open slowly so he won’t disturb Sam if he’s sleeping or not feeling well. But what he found was not a sleeping or sick Sam. What he found was a flushed and sweaty Sam sprawled our across his bed with three fingers buried in his ass. Dean stood there frozen just blinking at Sam before he finally came to his senses and covered his eyes with a quiet squeak. 

When he heard Dean in the doorway, Sam’s eyes flew open in shock. He saw Dean standing in the doorway with his hand over his eyes seemingly frozen. He picked up the closest thing he could find, which, unfortunately, happened to be a bottle of lube, and threw it as Dean. “What the fuck, Dean! Have you ever heard of knocking?” When Dean made no move to leave or response in anyway, Sam grabbed the book off his bedside table and threw it at Dean too. “God just leave already! Why are still standing there?”

Dean left without a second thought. No need to tell him twice. He left Sam’s room then took it a step further, and left the bunker entirely. He considered leaving the state too, but figured the bar in town would work just as well. 

As he settled into the bar with a drink in his hand, Dean wondered how something like that could even feel good. Realistically, he knew people did it. Hell, a few women had even allowed him to do it to them, but he’d never considered how it felt for them. Now that he was really thinking about it, he couldn’t believe anyone had ever let him do that. He couldn’t believe Sam was doing that to himself. He didn’t even know Sam was gay. 

After too many drinks, Dean decided to take an Uber home, and get Baby tomorrow. He may have been guilty of drinking and driving when he was younger, but dying over and over again makes you a little more cautious when you can afford to be. He was also making an effort to take Sam and Cas’ talk about making safe decisions more seriously. 

When he got back to the bunker, most of the lights were off and Sam’s door was shut tight. It was probably best to put off this conversation until tomorrow anyway. He went to his own room, and stripped down to his boxers before crawling into bed. 

When Dean’s head hit the pillow, he felt like he could pass out at any moment. He’d had a long day, and all the drinks were just heightening his exhaustion. Dean thought he’d be able to fall asleep quickly, but he couldn’t seem to get comfortable. He couldn’t seem to quit thinking about his baby brother with his fingers up his ass, and his dick was starting to get hard. He’d been hard on and off throughout the night, but his disgust with himself for thinking of Sam that way had helped to keep his erection away. 

Realizing he’s not gonna get any sleep unless he takes care of the issue, Dean shoved his boxers down to his knees, and started rubbing himself. He normally liked to tease himself and work up to it, but he was exhausted and trying to avoid thoughts of Sam. After ten minutes, Dean was no closer to his orgasm than he’d been when he started. 

He let his hand fall to the bed with a deep sigh. Not seeing any way around it, he reached into his bedside table and grabbed his bottle of lube. After slicking up his fingers, he hesitantly moved his hand between his legs until his finger could rub at his hole lightly. It felt weird but not bad so Dean slowly pushed a finger in while stroking his dick with his other hand. As he got more into it, he decided it didn’t feel bad, but it also didn’t think it felt good enough for anyone to ever do to themselves. Giving up, he pulled his finger out, and used that hand to play with his balls until he came. He passed out before he could even clean up his mess. 

Dean woke up the next morning feeling far less hung over than he should be. He tried to hide in his room for as long as possible, even considering peeing in the small bedroom sink at one point, but he eventually forced himself to act like an adult and left his room. 

After using the restroom and seeing that Sam’s door is still shut, he went to the kitchen to make breakfast. He’d just cracked his last egg when Sam walked in and immediately froze. Dean watched his brother stop in the doorway, and then turn bright red. His hair was messed up like he’d just slept for 12 hours, but the bags under his eyes told a different story.

Sam started to turn around to leave, but he stopped again when Dean cleated his throat. They stood awkwardly for another moment before Dean said, “I made breakfast. Stay and eat.” Sam hesitantly sat down at the table to join Sam for breakfast. Neither man spoke the entire time, but things had returned to normal by the end of the day. 

A few weeks and a few more failed attempts to finger himself finally made Dean willing to talk about what had happened. After a fifteen minute argument slash pep talk to himself, Dean walked into library with two glasses and a bottle of whiskey. He sat down at the table across from Sam, and poured them each a drink. Sam’s eyes flicked toward the glass, but he gave no other indication that he knew Dean was there. 

Growing impatient with Sam’s refusal to acknowledge him, Dean slid the glass toward Sam. “Drink up, Sammy.”

Sam reached for the glass, and closed his book with a sigh. “Alright, what is this all about then?”

“I can’t just enjoy a drink with my little brother.” 

Sam rolled his eyes before swallowing his drink in one big gulp. Dean did the same, and then refilled each of their glasses. Dean too stubborn and Sam too embarrassed, they sat in silence until Dean finally gave in. 

“I uhh... I didn’t know you were gay, Sammy.”

Sam rolled his eyes again and mumbled, “Not gay.” Dean snorted causing Sam to quietly add, “I’m bi not gay. I like both.”

Dean looked shocked to a second before whispering, “That’s a thing?” 

He said it said so quietly and so unsure that Sam’s stare to softened a bit. “Yeah, that’s a thing Dean. You can like both.”

Sam watched Dean try to process this new information. He looked like he was in the middle of a small crisis, and kept opening and closing his mouth like he couldn’t decide what to say. 

“Do you like both? It’s okay if you do.” Sam put his own discomfort aside to try to comfort Dean. 

“I don’t know... how’s it feel?”

Sam looked like he’d rather be anywhere but there. “I think that’s a question you should answer without me. It’s obvious I enjoy it, but not everyone does.”

A bright red color was slowly covering Dean’s face. “I did try, but I think I’m doing it wrong. It doesn’t feel bad, but it doesn’t feel good either.” 

“Well... um... you’re always going home with different women maybe you could try to hook up with a man instead?” Sam suggested unsure. 

“Or you could do it?” Dean looked shocked like he wasn’t sure how those words came out of his mouth, and he refused to make eye contact. 

“I... okay?” 

Dean quickly looked back at Sam. “Okay?” 

Both men stared at each other unsure of where to go from here. Dean repeated himself, but with more certainty this time, “Okay.” He poured them each a final drink before sliding Sam’s across the table. Then he stood up and headed toward his room with hopes that Sam was following him. 

Sam hesitated for a moment then followed him. By the time Sam got to Dean’s room, he was completely naked, and laying in the middle of his bed with a bottle of lube on the bed by his thigh. Sam took off his shirt so Dean wasn’t naked by himself, but kept the rest of his clothes on in an attempt to make it less weird. 

He slowly crawled into Dean’s bed, and settled between his legs. “Are you sure about this?”

Dean squeezed his eyes shut tight. “Yeah, Sammy, don’t be such a girl. Just shut up, and do it already.” 

Sam pinched Dean’s thigh, but otherwise didn’t respond. He opened the lube, and spread it over his fingers before moving his hand between Dean’s legs. “If you touch yourself while I do it, it will feel better.” Dean stroked his cock slowly, but gave no other indication that he was paying attention to Sam. 

Sam took a deep breath, and went for it. He started out slow by just rubbing his fingers over Dean’s hole to get him used to the feeling of someone touch him there. Dean flinched slightly at the first touch of Sam’s finger, but didn’t try to stop him. He kept stroking himself while Sam worked up to one whole finger then another. 

Dean still didn’t understand what all the excitement was about. Sure it didn’t really hurt, but it wasn’t exactly comfortable, and it certainly didn’t feel good. Dean was about to tell him to forget about it when Sam curled his fingers slightly making Dean feel like he’d been lit on fire in the best way possible. His eyes shot open, and he let out a strangled moan. 

“What the fuck did you just do to me?” He eyed Sam suspiciously. 

Sam smirked at him and curled his fingers several times in a row causing Dean to moan out again. “That’s the fun part. Don’t stop touching yourself.” 

Dean started stroking his dick again while Sam kept moving his fingers around inside of him. He didn’t hit that spot with every stroke, but he hit it enough to bring Dean right up to the edge without pushing him over. Dean’s hand kept slowing down on his dick because he was too distracted by Sam’s fingers. Sam could tell he was getting more and more frustrated. Deciding to take mercy on him, Sam slapped Dean’s hand out of the way and sucked the tip of Dean’s cock into his mouth. Sam flicked his tongue over the head of Dean’s cock while curling his fingers into that spot once, twice, three times, pushing Dean over the edge. Dean shot down Sam’s throat while yelling his name. Sam quickly shoved his own pants to his knees so he could get to his own cock. With a few strokes, he was shooting all over Dean’s stomach. 

Sam shoved Dean to one side of the bed, and collapsed next to him. Sam manhandled Dean’s body until his back was to Sam’s chest, and he was surrounded by the blanket and Sam’s arms. Both were content to spend the night together in Dean’s bed. They’d worry about the lines they had crossed tomorrow.


End file.
